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Synthesis and Copper(II)-Complexation Properties of an Unusual Macrocyclic Structure Containing α/β-Amino Acids and Anomeric Sugar β-Amino Acid

Abstract : A 16-membered macrocycle containing histidine, β-alanine, and an anomeric sugar β-amino acid was synthesised using a stepwise procedure starting from an exo-glycal derivative. This new macrocyclic structure contains an unusual carbonic carbamic anhydride moiety that was spontaneously formed upon saponification of the C-terminus ester group by attack of the resulting carboxylate group on the N-terminal benzyloxycarbonyl protecting group. This macrocyclic ligand formed a 1:1 complex with copper(II) ions in aqueous solution at basic pH. A structural study of this complex in solution was undertaken by UV/Vis, and paramagnetic 1H and 13C NMR spectroscopy. These spectroscopic data strongly suggest a {3 × Namide, NIm} equatorial donor set around the copper(II) ion, the fourth amide nitrogen being inaccessible for coordination, probably due to the rigid structure imposed by the sugar unit and the anhydride moiety.
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https://hal.univ-lorraine.fr/hal-01524707
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Submitted on : Thursday, May 18, 2017 - 4:48:40 PM
Last modification on : Friday, February 26, 2021 - 3:24:02 PM

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Anne-Sophie Felten, Nadia Pellegrini-Moïse, Katalin Selmeczi, Benoît Henry, Yves Chapleur. Synthesis and Copper(II)-Complexation Properties of an Unusual Macrocyclic Structure Containing α/β-Amino Acids and Anomeric Sugar β-Amino Acid. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2013, 2013 (25), pp.5645 - 5654. ⟨10.1002/ejoc.201300454⟩. ⟨hal-01524707⟩

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